


Roll Initiative!

by witchy_caswell



Category: High School Musical: The Musical: The Series (TV)
Genre: E.J. has stupid rolls, Gen, How Do I Tag, I Wrote This Instead of Sleeping, I promise, I wanted a dnd fic, I'm Sorry, Kourtney is a healer, There’ll be more chaos eventually, This has been floating around in my mind forever, but so do I, convince me otherwise, so enjoy this nonsense, so i wrote a dnd fic
Language: English
Status: In-Progress
Published: 2021-01-16
Updated: 2021-01-16
Packaged: 2021-03-14 09:14:26
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 3,597
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28793001
Author URL: https://archiveofourown.org/users/witchy_caswell/pseuds/witchy_caswell
Summary: Every single show needs a dnd episode and until Disney gives us one, I'm writing this nonsense.
Relationships: Everyone & Everyone
Kudos: 1





	1. What do you do?

Chapter one  
I tap my fingers on the worn box, waiting in the car for my mom. I have no clue if Carlos was this nervous before bringing his HSM board game to Ashlyn’s, but I am. I thought it would be fun to introduce them to DND, one of my favorite rpgs, at another cast party. Now I’m having second thoughts.  
“You ready?” My mom slides into the passenger seat. She needs to go to her book club, so I offered to give her a ride.  
“I guess,” I set the box full to the brim with characters, already rolled so we could start as soon as possible, dice, and all the d&d books I own and set off.  
After dropping Mom off, I head to Ashlyn’s house, basically internally screaming the whole way. Come on, Red. You can do this.  
When I pull up, it looks like everyone else is already here.  
“You can do it,” I mutter to no one “Just walk in there with your stupid game.”  
I knock on Ash’s bright orange door.  
“Big Red’s here!” she shouts as she opens the door. She glances down at my box “What’s that?”  
“A game,” I look down at my feet.  
“What type?”  
“A roleplaying game,”  
“Fun!” she drags me by my arm into the middle of the room. “And he brought a game!” she tells the rest of the group.  
That was easier than expected. I smile as I look around the room. My eyes fall on Ricky and EJ. They’re arguing over something, only they know what. This was a horrible idea. They’re gonna kill each other’s characters!  
“What’s it called?” Gina leans on the armrest of her chair.  
“Dungeons and Dragons,” I respond quietly.  
“What do you do in it?” EJ turns away from Ricky for a split second.  
I sit on the floor and start pulling dice out of the box. “Basically your characters go on a quest and the dungeon master helps you finish the quest and plays as the monsters you fight,”  
“I think I’ve heard of it,” Ashlyn sorts through the character sheets I brought “You already rolled characters?”  
“Yeah,” this is definitely getting easier.  
“Then let’s start!” she grins.  
“Who gets which characters?” Ricky moves over to sit by Nini.  
“I can explain each character and you each can choose like that,” I suggest.  
So everyone gathers around the small coffee table.  
“First there’s the fire spirit,” I start.  
After everyone has chosen their characters, I pull out my notebook where I wrote the entire story.  
“Carlos, you’re having a pretty usual day in town until you come across something strange outside of the city limits. You walk over to the glowing thing, you have no clue what it is, and start looking at it. Roll an investigation check.”  
Carlos picks up the gold twenty sided die. “This one?”  
“Yup!” I smile.  
It clatters on the wooden table, rolling around until it stops in front of Rico.  
“Seventeen,” he passes it back to me.  
“Alright,” I flip through my notes “With a plus one, you see that it’s a person, an elf to be exact. They’re unconscious and beat up like they had flown through the forest, hitting every tree on the way,”  
“Am I dead already?” Seb panics.  
“Nope,” I roll another die to scare everyone, something my dad used to do to me.  
“What happens next?” Nini looks over her character, a fairy mage.  
“That’s up to Carlos,” I answer “What do you do?”  
He sits there for a second, thinking. “Who else is in the town?”  
“Judging by the glowing elf, you should only go to Kourtney. Everyone else is against Magic Users,”  
“I’m a healer, right?” Kourtney starts planning something.  
“You are,”  
“Then you definitely should take them to me, I can probably heal them,”  
“Sounds good,” Carlos nods “I do that,”  
“Excellent,” I mutter “Kourtney, you’re working on one of your healing spells when your friend bursts into your house carrying a glowing body. What do you do?”  
“I use one of my healing spells,” she answers quickly.  
“Without asking any questions? He just randomly showed up with a body,” Natalie interrupts.  
“Fair,” Kourtney shrugs “I panic and ask him what the heck he’s doing with a glowing body,”  
“Should we talk as our characters?” Gina asks before Carlos can answer.  
“Definitely. That’s why it’s a role playing game,” I explain.  
Carlos nods. “I found them outside of town. I don’t know what happened, but they’re pretty beat up,”  
“Now I use my spell!” Kourtney grabs the d20.  
“Hold on,” I hold my hands up “You’re not going to use that one. You’re going to use the four sided one. After you roll that, add your spellcasting ability modifier to your roll. That’s how much life Seb gets back,”  
She drops the die on the table. “Four!” she exclaims and looks over her sheet “Plus two,”  
“Now you should be up to full,”  
As he adds Kourtney’s roll to his life, I pull Rico and Natalie aside.  
“You two are going to come into the house. You were looking for Seb and just tracked the thing that blasted him to here,”  
“Got it!” Rico nods and Natalie gives me a thumbs up.  
We make our way back to the small table.  
“So what happens next?” Ricky says, grabbing one of the pillows from the floor.  
“Seb,” I turn to him, “You wake up and see two humans standing above you. What do you do?”  
He hesitates. “I probably jump back and ask who they are,”  
I nod. “You jump up off of the floor. Pulling out your staff, you point it at the humans.” Pause, “Before they can answer, the door bursts open again,”  
“Again?” Kourtney shouts, “What the heck?”  
“Two figures run inside the house, ready to attack,” I say, before turning to Rico and Natalie, “You two followed a trail your friend left behind to this town. You find him in one of the humans' houses with two of them. What do you do?”  
“What are you doing?” Rico stands up and points at Kourtney.  
“And who are you?” Natalie adds on.  
“And now we’re going to see what’s happening with the others!” I say.  
“Seriously?” E.J. groans, dropping his character sheet.  
“I mean,” I hand it back to him, “I was going to let you do some stuff, but maybe not,” he doesn’t answer, “Now, let’s see what’s happening in the forest…”


	2. Who, what, where?

**Summary for the Chapter:**

> It’s literally just chaos and me projecting on to Big Red. Enjoy the weirdness, my dudes.

**Notes for the Chapter:**

> It happens towards the end, but Red is master of dungeons and Gina is ew feelings. Hopefully everyone else will get in the chat eventually.

Chapter two

“Nini, you’re flying through the forest when Ricky runs up to you,” I start, “He says that Rico, Natalie, and Seb are missing. What do you do?”  
She thinks for a minute. “My character doesn’t know what happened with everyone else, right?”  
“You’re character wasn’t there,” Ash says, “So she doesn’t know,”  
“Exactly,” I nod.  
“So I suggest we go look for them,” Nini starts planning something, “See if we can find any clues,”  
“That sounds great!” Ricky smiles at her.  
“Where am I?” E.J. asks, “You said I’d get to play soon?”  
“And just then,” I say, “E.J. comes into the clearing you two were planning in. He’s holding some sort of message and waving it at you,”  
“What is it?” Nini asks.  
“I have no clue,” E.J. answers.  
“Let me explain,” I laugh, “It’s a message he found by the elves’ town, it says that your friends were chasing a monster that attacked the town and that they’d hopefully come back tomorrow,”  
“Then we don’t need to worry!” Ricky says, “They’re fine,”  
“We’re really not,” Rico shrugs.  
“But our characters don’t know that,” he continues, “So we can’t do anything about it,”  
“Maybe we should check with Ashlyn?” Nini tries to keep going, “Maybe she saw something,”  
“That’s a great idea,” Ashlyn says.  
“So you head to the treehouse that the forest spirit lives in,” I start.  
“I live in a treehouse?” she exclaims, “that’s awesome,”  
“At least you don’t live where these crazy people keep storming into,” Kourtney laughs.  
And soon everyone is laughing. Why was I thinking that this would be bad? This is amazing!  
Then I remember how my old friends made fun of me for liking stuff like this. They thought it was stupid to roll dice and fight goblins, only because of the pen and paper aspect. If it was a video game, they would have been all over it.  
Don’t get me wrong, I love video games, but something about drawing maps that my friends would explore and having no restrictions on what you can do just makes DND that much better to me.  
And that’s why I’m glad Ricky dragged me into the group. They haven’t made fun of me like my old friends did yet and they’ve been ready to try anything someone in the group puts out there.  
“So,” Nini interrupts my thoughts, “What does Ashlyn know?”  
I stumble over my words for a minute before answering. “Ashlyn tells you about a dark shadow creature that she saw by the Elves’ town. A while later she saw Seb chasing it away from the buildings. After a flash of light, he was nowhere to be seen. Then Rico and Natalie went running away, towards the Human settlement,”  
Everyone’s quiet.  
“Then that’s where we should go!” Ricky breaks the silence, “It’s our only lead,”  
“Can I come? I love a good quest,” Ashlyn says.  
“We need all the help we can get,” Nini nods.  
And everyone is trying to figure out what the shadow thing was and what happened to Seb.  
I look over the group. And it’s crazy. This is one of the first times I’ve seen Ricky and E.J. getting along, Natalie talking to the whole group instead of only a select few, and at least a very small amount of drama within the whole group.  
It’s exactly how I dreamed of playing with someone when I was younger. Someone other than my parents anyway.  
One of the clocks chime.  
“How is it that late already?” Gina grumbles at the clock.  
“Time flies when you’re having fun,” Ashlyn says.  
Everyone clears out. I start cleaning up my dice and the character sheets. Ash comes and sits by me.  
“Are we going to play again?” she asks.  
“Hopefully,” I drop one of the dice. Heck, “I could ask my parents if we could play at the shop one day if everyone’s able to,”  
“That sounds great,” she grabs the last golden die and puts it in my bag, “And I know that everyone is dying to play again. That was the first time I’ve seen us hang out without some crazy drama,”  
“Definitely,” I nod, “I’m pretty sure that was the longest time Ricky and E.J. have gone without trying to kill each other,”  
She laughs. “But for real, that was a lot of fun. You’re an excellent dungeon master!”  
As I finish packing up, she walks away, talking to Gina.  
And I leave.  
“Off to pick up Mom,” I whisper to myself.  
It seems to take forever, but I finally arrive.  
My mom steps into the car.  
“How was the party?” she asks, “Did they like your game?”  
“It was amazing,” I pull out of the driveway, “And they loved it.”  
“That’s great,”  
“Yeah,” we drive in silence for a minute, “I actually wanted to know if they can come to the pizza shop to play again sometime?”  
“Of course!”  
We climb out onto our slightly steep driveway.  
Once I’m inside, I pull out my phone and message the group.

WILDCATS

master of dungeons has renamed the chat to FANTASY WILDCATS

master of dungeons: hello travelers. i have an announcement to make. we will be playing dnd again at my parents pizza shop whenever everyone is available.

ew feelings: so that’s why you’re named that.

ew feelings: makes sense.


	3. Pizza and Dragons

**Summary for the Chapter:**

> And so, the plot begins.

**Notes for the Chapter:**

> Even though not all of them appear, here are the chat usernames!   
> Master of dungeons- Big Red  
> Ew feelings- Gina   
> Bumblebee- Nini  
> Duhhricky- Ricky  
> Witchy_Caswell- Ashlyn  
> GrimGrinningGhost- Kourtney  
> Betelgeuse- Seb  
> King_George- Carlos  
> Pinetree- E.J.  
> TheDemonCrowly- Rico  
> Alnilam- Natalie

Chapter Three  
“I have been waiting for this day for a long long time!” Ricky paces around my room. I have no clue what he’s doing, “Can you tell me what happens?”  
“First of all,” I start, “It’s only been a few days. And second, I will not tell you anything until you’re facing the monsters,”  
“So there’ll be monsters?”  
“Most likely,”  
Before Ricky can ask me any more questions, my mom calls down the stairs. “Are you two ready for school?”  
“Yeah!” I shout back before grabbing my bag.  
“I don’t know if I can wait the whole day!” Ricky pretends to fall over, “I need to know!”  
“Let’s just go,” I laugh at my friend.

***

The rest of the day passes pretty quickly. Both E.J. and Ricky have been pestering me all day, trying to find out what happens next.  
We decided to meet at the pizza shop today after rehearsal was canceled for another reason that I don’t know.   
So we all made our way to the shop, after picking up quite a few things.  
“Is all of that really necessary?” Ricky laughs at my collections of boxes.  
“Yup,” I shove it into the trunk, “You never know if you’ll be fighting a fire dragon or an elemental spirit!”  
He looks at me like I’m crazy before driving away.  
For some strange reason, probably the large amount of boxes I had to find, we’re the last ones to arrive.  
We walk into the warm building. I scan the tables for our friends. They pushed most of the tables together in the center of the main room. And it’s really loud. The only conversations I can pick out are Kourtney and Ashlyn talking about ghosts and most of the table arguing over Beetlejuice. Who knows what that’s about.  
“Big Red’s here!” Nini jumps up from her spot at the table.  
“Wow,” Ricky says as he sits next to her, “Thanks for mentioning me!”  
“Let’s just play,” Nini rolls her eyes at him.  
After setting up the new map I drew, I start to recap our last game. “When we last left our heroes, Ricky, Nini, and E.J. found out where their friends could be with the help of Ashlyn. And their friends are in a bit of a predicament as they find themselves surrounded by humans,” everyone looks excited. It still blows me away that because of the game, Ricky and E.J. can sit at the same table without shouting at each other, for now. They still have time, “So, Rico and Natalie, you just barged into a human house to save your friend. And I need everyone in that house to roll initiative!”  
“They need to fight each other?” Ash laughs.  
“Wait, what?” Carlos exclaims.  
“Why do we need to fight?” Kourtney joins Ashlyn in laughing, “What did we do?”  
“If you look at it from Rico and Natalie’s point of view,” I answer, “Their friend was just blasted across a forest and is now in a human house. They’re probably going to fight. But, Kourtney and Carlos, you two can try to use your turns to convince them not to attack,”  
“Then don’t attack us!” Kourtney says.  
“I’m afraid that’s not how that works,” Rico explains, “You actually have to take turns taking actions. And to settle the order, we need to roll a d20,” Everyone looks at him, “What? I did my research,”  
I make a note to talk to him later. That was definitely awesome. “Exactly. So if you guys could roll the dice, that would be great,”  
The golden dice clatter on the wooden tables. Once they come to a stop, they start shouting out numbers.  
“One at a time,” I pull out my notebook to keep track of the rolls, “Alright! Natalie is going first with her eighteen,”  
“Heck yeah!” she shouts. I’m really glad that business is slow today, everyone is really chaotic and loud right now.  
“So,” Nini bounces in her seat, “What do you do?”  
Natalie thinks for a moment. “How do I sneak attack?”  
“One of your teammates has to be next to the enemies,” I point to the map as I set out everyone’s figures. They’re actually just drawings I did last night based off of their actual appearances, “So you could do that, both Rico and Seb are next to the others,”  
“Then I sneak up to Kourtney and use my sleep bomb thing!” she grins.  
“How did you get that?” Ashlyn asks, “We only have basic equipment, right?”  
“I have literally nothing else. Just a few sleep bombs and a knife,” Natalie shrugs, “They seemed cool,”  
“So you run up to the healer and drop one of your bombs,” I recap, “Do you disengage?”  
“That sounds like a good idea,” she nods, “I do that,”  
“Kourtney, roll a d20!” I laugh. This is amazing. Much better than anyone else I’ve tried to start a game with, “If you get it higher than Natalie’s roll, you stay awake. If it’s lower, you fall asleep,”  
“Please don’t kill me,” Kourtney says with a straight face, rolling her die, “Eight. Goodbye friends, I will be falling asleep soon,”   
“We’ll see,” Natalie drops the die, “Fourteen!”  
“Great,” Kourtney laughs, “I am now dreaming,”  
“Carlos, you just saw two elves run into your friend’s house. One of them runs up to her and after a burst of smoke disappears, she’s on the floor,” I explain the crazy scene.  
Pause.  
“Now, if she was still awake, it would be Kourtney’s turn, but as she’s on floor, Seb,” I continue, “It’s your turn,”  
He looks over his character sheet. “I cast freeze,” he starts smiling.  
“Alright, roll the die,”   
He rolls it and it falls off of the table.  
Gina picks it up. “Twenty!” she shouts.  
“Everyone in the house is frozen!” I say, “Do you say anything?”  
He stutters.  
I decide to message him what happened to his character.

master of dungeons- you got blasted into the town by the shadow knights, if that helps

betelgeuse- alright! does my character know that?

master of dungeons- yup

Seb puts his phone down and starts to talk.  
“Rico, Natalie,” he glares at the duo, “These people saved me from the Shadow Knights. I trust them,”  
“What are Shadow Knights?” Ricky asks.  
“You’ll see,” I say, “You’ll see,”

**Notes for the Chapter:**

> If you want the meanings behind everyone’s usernames, just let me know!


	4. In The Forest

**Summary for the Chapter:**

> Gina finally appears though it seems her character wants something, E.J. fails a roll and almost walks into a tree, and Big Red is enjoying this chaos.

**Notes for the Chapter:**

> I'm back!! I have no clue if people are reading this, but I'm planning to add some drama soon! So stay tuned.

In the Forest  
Chapter four

“We need to find out what those things are,” Ashlyn laughs, “If they’re what I think they are, they’re going to be a pretty major part of the story,”  
“That would make sense,” Carlos adds on, “If they’re the weird shadow Rico and Natalie saw, then they’re definitely a big part of whatever we’re supposed to be doing,”  
“Well,” I turn to the second group, “We need to figure that out. Where are you guys going?”  
“As far as I know,” Ricky says, “We’re going to the human town Rico and Natalie left to,”  
“Do we even know how to get there?” Nini asks, flipping through her character sheet again.  
“How can we find out?” Ashlyn says, starting to plan their next move.  
“Nini can try using her tracking skills to find out where they went,” I answer.  
“I do that,” she grins, grabbing the d20, “I roll this one, right?”  
“Yup!” I nod, “Just roll that plus your survival plus.  
“Alright,” she drops the gold die on the wooden table. It clatters to a stop, “Sixteen plus three!” she starts bouncing again.  
“With that roll, you see not just a few footprints on the ground, but also a path through the trees where it looks like someone was blasted through them,” I lower my voice as the door opens. A family walks in, “Do you follow the path?”  
“Yeah!” Ricky exclaims.  
“Let’s go!” Ashlyn says.  
“Your small team of magical creatures and magic users hikes through the forest, following the small fairy to the human town. As you creep across the moss-covered ground, you hear shouts coming from ahead,” I say, “Multiple voices are shouting before they all go quiet,”  
“Who are they?” E.J. asks.  
“Also when do I come in?” Gina starts drumming on the table.  
“First, you’ll need to either roll an investigation check or just go find where the voices are coming from. Second, I’ll explain that in a moment,” I answer both questions.  
Everyone quiets down for a bit before E.J. starts to grab the die.  
“I try to listen to what the voices are saying,” he rolls the die and it crashes into one of the character tokens.  
“Three,” he grumbles.  
“You hear nothing,” I say, “Except for the wind whipping around the forest. You look up and see someone laughing at you. That usually isn’t that strange, except for the fact that the person is floating above your head,”  
“There I am!” Gina laughs.  
“Gina,” I try to sound as dramatic as I can, not exactly my strong point, but it’s somewhat necessary for this, “You’ve been following these questers for quite a while, seeing how long it would take for them to notice. And one of them is trying to listen to some voices in the human town but just started walking in the completely wrong way, while humming very loudly,”  
Everyone starts laughing.  
“Hey!” E.J. shouts.  
“You did roll a three,” Nini says, trying to catch her breath.  
“So,” Gina falls into character, “Do you want to hear what they’re saying, or not?”  
“Please help us,” Ashlyn responds after a few moments.  
“Fine,” Gina shrugs, a smug grin spreading across her face. I guess this is what I get for playing DND with a bunch of actors, “But I’ll need something in return,”


End file.
